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Penny is the social glue of these friends. Always quick to offer advice to either Alex or Dave about the ups and downs of dating as she is well-versed in the single dating culture of the new decade. She works for a public relations firm and prides herself on being the most stylish person in the office. Penny and Max have been best friends since college and provide each other a shoulder to lean on.

In the pilot episode, Penny is a member of the friendship group also including Jane, Dave, Max, Alex and Brad. At her birthday Penny claims to be Jewish and is celebrating her twenty sixth, but she is lieing to impress her new boyfriend Todd. Later, she confesses that she is Cathloic, and that she is actually thirty. She decides to end her relationship with Tom after the many hints from Max that he is gay.

In the second episode, Penny starts a friendship with a stereo-typical gay man, Derek. But she later ends their friendship after feeling it was messing with the groups dynamic. Max tells Penny that she is the 'stereo-typical gay man' of the group.

In the third episode, Penny encourages Alex to go on a date with Malcolm. However, when Penny finds out that he is a squatter who is living in Max's apartment, she along with Dave and Max gatecrash their date. Alex and Malcolm decide not to take their date any further.

In the fourth episode, Penny meets the man of her dreams on a blind date, who she later finds out happens to have a rather infamous last name, Hitler. She attempts to get used to the name by imaging if they married what her name would appear like. However, Doug finds out and thinks that Penny is a hilter fan, ending their doomed relationship.

In the opening episode of season two, Penny buys a new apartment and fears it may be cursed after numerous amounts of cats show up, episodes of the view are recorded on the tv and single pizza offer is posted through her door, she fears she may die alone like the previous owners. She throws a roaring 20s party by fails to dress up but during the party she comes to her senses and realised the condo isn't cursed. Later Alex moves in.

In the secound episode 'Baby Steps.' Penny reveals she use to pretend she was Mexian in high school so the popular girls wouldn't pick on her. She then starts hanging out with some high school girls at Alex shops, one of their brothers she has a huge crush on since high school but he only dated 'college girls.' Later Penny is ditched by them and revealed he still only dated 'college girls.'

In the third episode. Penny's perpetually optimistic mom, Dana, is in town for a singing gig at a boat show. Her enthusiasm inspires the gang, but Penny she's getting a divorce, she decides it's time to give mom a reality check, leading to her mum giving up but later Penny comes to her rescue and they perform together at the boat show.

In the fourth episode Penny has a crush on a local bar tender Tyler. Jane convices her to make a mood board but when disapointed that it wasn't coming true Jane tries to make it happen. When Alex tells Penny this she asks for more to see if Jane will do more including tickets to Greece. Penny later has a go at Jane but Jane confessed she did nothing to make Tyler ask Penny out.